Try clicking on your ipod icon, and selecting the tab to automatically sync. This should sync your ipod automatically every time you connect it to your computer with whatever new music, videos....etc that you have on itunes.
No no, thats not the problem. It's just that itunes doesn't recognise the playlist and put it in the ipod area. I made a new playlist, but still doen't pick up.
I think it's got something to do with my music TBH. We recently got the hard drive wiped from a virus, so only some of the music in my libary is still available...
